How Not to Date

Anyone can tell you how to date online, I’ll tell you what you’re doing wrong.

By Judy McGuire

You don’t have to be yourself, but don’t be Miranda July.

Nobody expects (or wants) you to lay your soul bare the first time you make contact, but please avoid channeling your inner manic pixie dreamgirl/boy. Last weekend, in the midst of our city’s second biggest snowfall in history, a dullwitted twentysomething guy contacted a friend and posed the question, “If today were a color, what would it be?” Derp. There are very few people who can pull off “quirky” with charm and humor. Unless you’re Amy Sedaris, you’re not one of them.  

A headshot does not mean a “head of your penis” shot. 

Unless specifically requested, please don’t send out closeups of your taint, testicles, foreskin, schvantz, chocolate nickel, vulva, or browneye. (And if you’re not going to heed this advice, at least make sure your bits are clean and reasonably groomed before you click “send.”) In case you were wondering, headless body shots tell your potential prey that you’re either married or have a serious case of butter face. Men, unless you’re built like Idris Elba, your topless photos generally provoke an eyeroll. Ladies, as long as you’re fine with them being distributed amongst all his friends, boob shots are always welcome. 

Carpet-bombing is not an effective technique

Sending out dozens (or hundreds?) of one-word emails is not going to get you laid. Or at least not laid well. I’m not trying to go all Miss Manners, but anyone who bothers responding to a message that simply reads, “Hey!” is probably as stupid and desperate as the person who sent it. Instead, take a second, read the person’s profile, and reference it in your message. It may take three minutes longer, but it increases your chance of an answer by 400%*. 

If you’re going to lie, lie prudently.  

By now, most online daters are willing to accept a certain amount of fudging in a profile. Shaving off two or three years—fine. Two or three decades? Congratulations, you just won the Saddy McOldPerson Award. Likewise, those apps that blur the wrinkles away aren’t fooling anyone, nor is the Photoshop “stretch” tool going to help once you meet in person. It is possible that nobody will notice if you deduct six pounds from your weight, but six inches—regardless of where that six inches is located—is not going to go unnoticed.

Everyone knows about negging, so just don’t. 

Insulting someone in a lame ploy to pique their interest is about as clever as stepping on a warm turd with your bare foot. And that isn’t a neg; that’s a fact.  

Speaking of negativity. . . . 

Do you really think other people just forgot to write that they’re not looking for “game players” or “crazy broads?” There’s really no need to specify what you’re not into unless someone asks. When you list a whole bunch of dealbreakers, you’re making it clear that you’ve got a cargo hold’s worth of baggage and you’re probably a bit of a whiner to boot. 

*That is a guesstimate with no backup science, but it seems likely.

Published January 28th, 2016


Judy McGuire is a freelance writer and the author of The Official Book of Sex, Drugs, and Rock ‘n’ Roll Lists and How Not to Date. Send your dating questions here and she’ll attempt to straighten out your love life.